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Asian Journal of Chemistry Asian Journal of Chemistry Asian Journal of Chemistry; Vol. 26, No. 14 (2014), 4445-4448 ASIAN JOURNAL OF CHEMISTRY http://dx.doi.org/10.14233/ajchem.2014.16897 Chemical Composition, Antifungal Activity and Toxicity of Essential Oils from the Leaves of Chimonanthus praecox Located at Two Different Geographical Origin † † * * * REN-YI GUI , WEI-WEI LIANG , SHENG-XIANG YANG , LI LLU and JIAN-CHUN QIN College of Plant Science, Jilin University, Changchun, Jilin 130062, P.R. China; The Nurturing Station for the State Key Laboratory of Subtropical Silviculture; Zhejiang Provincial Key Laboratory of Chemical Utilization of Forestry Biomass, Zhejiang A&F University, Lin'an, Zhejiang 311300, P.R. China *Corresponding authors: E-mail: [email protected]; [email protected]; [email protected] †Contributed equally to this study Received: 19 December 2013; Accepted: 24 February 2014; Published online: 5 July 2014; AJC-15493 The composition of the essential oils obtained by hydrodistillation of different geographical origin of Chimonanthus praecox, including Hangzhou and Wenzhou samples, were investigated by GC/MS. Forty three components comprising 93.05 % of the leave oils from Hangzhou plant, and 32 components comprising 94.26 % of the leave oils from Wenzhou plant were identified. The major components in the leaf oil from Hangzhou samples were (-)-alloisolongifolene (10.20 %), caryophyllene (9.31 %), elixene (8.52 %), germacrene D (7.30 %), germacrene B (7.44 %), δ-cadinene (6.17 %) and β-elemen (4.67 %). While, the oil from Wenzhou samples contained furan, 3-(4,8- dimethyl-3,7-nonadienyl)-, (E)-(21.69 %), eucalyptol (19.02 %), terpilene (12.41 %), p-menth-1-en-8-ol (6.65 %) and geraniol (5.29 %) as the major components. The antifungal activity of the oils against 8 phytopathogenic fungi was tested by determining minimum inhibitory concentrations using the microdilution method. Both oils exhibited potent antifungal activities with MIC values of 8-32 µg/mL. Both oils were considered bioactive, showing an LC50 value of 30 and 22 µg/mL in the Artemia salina lethality test. Keywords: Essential oils, Composition, Antifungal activity, Toxicity, Chimonanthus praecox, Geographical origin. INTRODUCTION knowledge, the essential oil composition of this medicinal plant has been studied thoroughly and hundreds of components have Since ancient times the crude herbal extracts of aromatic been identified up to date9-14. Generally it is accepted that vari- plants have been in use for different purposes, such as food, ability of chemical composition of essential oil of C. praecox drugs and perfumery1. The essential oils are considered among depends of geographical origin and stage of plant development. the most important antimicrobial agents present in these plants, Thus, there is still a considerable research interest in the and may also have antioxidant, insecticidal, antifungal, anti- assay of composition and biological properties of essential oil bacterial, cytotoxic and antiinflammatory activities2,3. of C. praecox from different geographical origin. In the present C. praecox belonging to the Calycanthaceae family are work, we have investigated the essential oil composition of deciduous shrub native to China, which has survived from the C. praecox cultivated in Hangzhou and Wenzhou. In addition, tertiary period. They are famous traditional fragrant flower the aim of this study was to assess the antifungal activity and plant with high ornamental value in China. It is also traditional toxic activity of the isolated essential oil, which have not been Chinese herbal medicine for the treatment of colds, analgesic, reported to date. coughs, asthma and other disorders4. Therefore, C. praecox have EXPERIMENTAL been phytochemically and pharmacologically investigated and many molecules have been isolated and identified. In this The fresh leaves of C. praecox were collected in Hangzhou context, different classes of organic compounds of medicinal and Wenzhou of Zhejiang province, China. Botanical identi- interest have been reported, mainly including alkaloids and fication was carried out by Prof. Li Gengyou. Voucher speci- sesquiterpenoids5-7. mens (no. 0270012 and 0270010) of the samples have been In recent years, research and development of essential oil deposited with Plant laboratory of Zhejiang A & F University. products of Chimonanthus plants have been more and more Isolation of essential oil: The different original dried leave attended, due to excellent aroma8. Moreover, to the best of our of C. praecox were subjected to hydrodistillation for 5 h and 4446 Gui et al. Asian J. Chem. 5 h, resp., using a clevenger-type apparatus. The obtained oils artificial light around the clock. Larvae after 48 h were were dried (anhydrous Na2SO4) and stored in sealed flasks at extracted and counted using a Pasteur pipette. A standard 4 °C. solution of 1,000 µg/mL was prepared with 100 mg of essential Gas chromatography/mass spectrometry (GC/MS) oil diluted in 1 mL of DMSO, and the volume was completed analysis: Gas chromatography/mass spectrometry analysis was with sea water in a 100 mL volumetric flask. Concentrations carried out using splitless injection mode on a Varian CP3800/ of 900, 100, 10 and 1 µg/mL were prepared using standard 1200L GC-MS instrument with a fused silica capillary DB-5MS solution. For each concentration, 10 brine shrimp larvae were column (5 % phenylmethylpolysiloxane, 30 m × 0.25 mm, used, placed in flasks that were filled with seawater to a total film thickness 0.25 µm). Helium was used as the carrier gas, volume of 5 mL. Intermediate concentrations were made to at a flow rate of 0.8 mL/min. Oven temperature was progra- calculate the LC50. For the control group, a solution was mmed at 45 °C for 3 min, then 45-90 °C at 10 °C/min, then prepared with 100 µL of DMSO and 4.9 mL of seawater. After 90-180 °C at 6 °C/min, then 180-230 °C at 12 °C/min, then 24 h, the dead larvae were counted and the LC50 value was 230-250 °C at 9 °C/min and finally held at 250 °C for 9 min. estimated using the Origin 9.0 statistical program. The injector and detector temperature were set at 250 °C and RESULTS AND DISCUSSION 280 °C, respectively. The electron impact source was 70 eV, ion source temperature was 200 °C, the mass range 33-450 Gas chromatography-mass spectrometry analysis of amu and the scan rate was 0.5 s. essential oil: The detailed composition of the essential oil of The components of the essential oils were identified by C. praecox fresh leave from Hangzhou and Wenzhou is comparison of their RI (retention indices) relative to C5-C24 reported in Table-1. Overall fifty compounds were identified n-alkanes obtained on a nonpolar DB-5MS column, with those in the fresh leave of C. praecox. For easier comparison of the provided in the literature, by comparing their mass spectral oils, the components were grouped into five classes: mono- fragmentation patterns with those of similar compounds from terpene hydrocarbons, oxygenated monoterpenes, sesquiter- databases (NIST and Wiley Mass Spectral Libraries) and reported penes hydrocarbons, oxygenated sesquiterpenes and others. in published articles. For each compound on the gas chroma- However, monoterpenes and sesquiterpenes were the main togram, the percentage of peak area relative to the total peak compounds identified. As outlined in Table-1, the GC-MS area of all compounds was determined and reported as relative analysis of the oils in the Hangzhou and Wenzhou branch amount of that compound, without using correction factors. revealed the identification of 43 and 32 components, respec- Antifungal bioassay: The test phytopathogenic fungi tively, representing 93.05 and 94.26 % of total oils. All oils used in this study were Botrytis cinerea, Fusarium grami- showed some similarity in the qualitative composition, but they nearum, Fusarium avenaceum, Cylindrocarpon destructans, differed significantly from a quantitative point of view, showing Helminthosporium turcicum, Colletorichum gloeosporioides, some differences in their main constituents (Table-1). The Sclerotinia sclerotiorum, and Monilinia fructicola. All the fungi quantity of the chemicals in the oils from Hangzhou was more were isolated from infected plant organs at the Zhejiang A&F than the oils from Wenzhou. The major constituents of C. University. praecox essential oil were (-)-alloisolongifolene (10.20 %), Antifungal activity was assessed by the microbroth dilution caryophyllene (9.31 %), elixene (8.52 %), germacrene D method in 96-well culture plates using a potato dextrose (PD) (7.30 %), germacrene B (7.44 %), δ-cadinene (6.17 %), and medium15. The serial doubling dilution of the essential oil and β-elemen (4.67 %) for the Hangzhou samples, whereas the oil its major compound was prepared in DMSO, with concentra- obtained from Wenzhou plants was characterized by a higher tions ranging from 0.25 to 32 µg/mL. Final concentration of level of furan, 3-(4,8-dimethyl-3,7-nonadienyl)-, (E)-(21.69 DMSO never exceeded 2 %. A commercial fungicide carben- %), eucalyptol (19.02 %), terpilene (12.41 %), p-menth-1-en- dazim (Aladdin Chemistry Co. Ltd.) was used as positive 8-ol (6.65 %) and geraniol (5.29 %). These results showed control, and the solution of equal concentration of DMSO was that the 2 samples mainly contained large amounts of mono- used as a negative control. The tested fungi were incubated in terpene hydrocarbons and sesquiterpene hydrocarbons. But the potato dextrose medium for 18 h at 28 ± 0.5 °C at 150 rpm, there were some differences in the main compounds between and spores of different microorganism concentrations were the two samples. The variance observed in the leaves essential diluted to approximately 1 × 106 CFU with potato dextrose oils composition could be related to several factors, including medium. The test oils (10 µL) were added to 96-well micro- physiological variations, environmental conditions-climate, plates, and 90 µL of potato dextrose medium was added. Serial pollution, diseases and pests, edaphic factors, geographic dilutions were made in the 96-well round-bottom sterile plates variation, genetic factors, and amount of plant material/space in triplicate in 50 µL of potato dextrose medium, and then and manual labor needs17.
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